The city's oldest surviving bridge, first built in wood in the Middle Ages, rebuilt in stone to Antonio Cortázar's neoclassical design and inaugurated in 1872. It marks the historic frontier between the old walled town and the working east bank across the Urumea.
Rafael Moneo's two tilted, translucent glass cubes — nicknamed "two stranded rocks" — built on the rubble of the grand casino that once gave this site its name. Opened in 1999 and awarded the Mies van der Rohe Prize in 2001, the Kursaal is now the beating heart of San Sebastián's Film Festival and the city's culture-led reinvention.
Zurriola is the beach San Sebastián re-engineered in the 1990s, adding a breakwater and imported sand to tame a dangerous stretch of shore into 800 metres of open, east-facing surf beach. Surfers claimed it as their capital, and today it's the beating heart of young Gros.
The sunset end of Zurriola where the promenade dies at the foot of Monte Ulia, watched over by Nestor Basterretxea's steel Dove of Peace (Bakearen Usoa, 1988) and claimed every evening by half of Gros for the ritual of watching the light go down over the bay.
The locals' pintxo grid on Calle Zabaleta and Peña y Goñi, where Bar Bergara's award-winning counter, Bodega Donostiarra and Hidalgo 56 serve food 10 to 20 percent cheaper than the Old Town with no tourist queues. On Thursday nights the whole neighbourhood spills out for pintxo-pote, a pintxo and a drink for around two euros.
The Belle Époque gateway where the Paris train met the resort: the 1864 Estación del Norte and the 1905 María Cristina bridge, its four obelisks copied stone for stone from Paris's Pont Alexandre III. This was the river as red carpet, where royalty and film stars stepped off the train and crossed west to the glamour.
A monumental 1913 tobacco factory where thousands of women rolled cigars for ninety years, reborn in 2015 as Tabakalera, the city's International Centre for Contemporary Culture. Its severe brick facade and vast internal spaces now house free galleries, the Film Festival's offices, and a rooftop with one of the best views in town.
Cristina Enea is San Sebastián's largest and wildest park, created from the private estate the Duke of Mandas willed to the city; its lawns are home to peacocks and its grounds hold giant redwoods and cedars, with the duke's former palace now serving as an environmental resources centre.
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